Food & Drink

FOOD + TRAVEL: Eat Your Way Through Chicago

by Winston "Stone" Ford


It’s official. I’ve gained at least 10 pounds thanks to my trip to Chicago.

My skinny jeans no longer fit anymore. My gut has returned, and I’ve been living in comfortable sweatpants for the past couple of days. And honestly, can you blame me? Chicago is a food town. Honestly, it’s a food paradise. But honestly this is nothing new, the city has retained it’s “Food Town” moniker for years now. However, for people on the East and West Coasts, the Chi is still kind of in flyover territory. This is sad.

The Chi, with all of it’s problems, is a great, if not segregated city. The thing that I like about this city is that unlike NYC, food is not a “thing” here. Good food is just expected. In NYC we expect to be wowed.

With said high levels of expectations comes some of the best restaurants in the country.

Boozy Brunch at Rodan


This is how you do brunch. Sure, the unlimited mimosa “boozy brunch” is getting played out, but at …. the champagne is delivered bottle service style to your table for only $10. Couple that with random Italian sci-fi films being shown on the big screen and you get a perfect way to spend your Saturday afternoon. Their Asian-themed breakfast specialties aren’t bad either. Unlike a lot of brunch spots in Wicker Park, this place doesn’t have a crowd, so just walk on in.

1530 N Milwaukee Ave (at North And Damen)

Topo Gigio Ristorante

Just like Georgetown or the Upper West Side, Old Town is a bit too “old money” for my tastes, however we ended up stumbling upon this spot, ….. The portions are big and they encourage sharing, which makes it perfect for a date.

1516 N Wells St (btwn North Ave & Schiller St)

Bongo Room


Remember that game Never Have I Ever? Well, it applies here. Never Have I Ever woke up at 9 in the morning to go to brunch. Having that said, going to … was well worth it. Let’s keep it real here, this is like having dessert for Breakfast. Their pancakes are not pancakes per se, but basically cake smothered with gooey frosting in place of syrup. Their Red Velvet and Cheescake pancakes are wonderful, and this spot gives a whole new meaning to the word “itis.”

Get to this place early. The line forms before 9, and there is usually a 30 minute wait even at 8:30 AM.

1470 N Milwaukee Ave (at Honore St)

Lou Mitchell’s


Located near the beginning of Route 66, spot is a Chicago institution. Everyone gets fresh doughnuts on the way in and ladies get Milk Duds for their lady-ness. The spot serves up nothing special, the food is straight ahead diner fare. However, it’s one of those “down home” places that every city has, and that we all should support.

565 W Jackson Blvd (btwn S Jefferson St & S Clinton St)

The Girl and the Goat



I’m really not impressed by celebrity restaurants but I had to make an exception for The Girl and The Goat. The brainchild of Top Chef winner Stephanie Izard, the restaurant serves farm to table tapas with three very unique combinations. To begin you choose a meat, fish or vegetable plate, tapas style and dig in. Usually 4 plates should be enough for 2 people, though the portions are larger than most we were barely able to finish them. This is a rarity—everything on the menu was GOOD. Like my Lord you can taste every spice on the plate. This is no doubt a foodie’s paradise.

This is one of the most popular restaurants in Chicago, so reservations fill up 2 months in advance. HOWEVER if you come right when the restaurant opens (around 4:30-5pm) you should be able to get a table (limited to an hour and a half) or a bar set. Honestly, it’s worth it.

809 W Randolph St (at Halsted St)



In New York, a speakeasy is usually a tiny ass bar in the back of a restaurant with 12 stools and a pretentious attitude. Chicago, however, contains the mother of all speakeasies. Although the entrance is a small door, this spot is pretty easy to find. Once you get downstairs, you’re greater with several rooms of greatness. There is a restaurant, performance space (with nightly jazz and burlesque shows), a whiskey “library” (which boasts the largest collection of American whiskey in the country) and supposedly an outdoor space. This spot is huge, and during the week, not that busy, so you can stretch out and chill.

111 W Kinzie St (btwn N LaSalle St & N Clark St)


Travel Facts

Get In: The Chi is served by two airports, so the city features ample flights from both coasts. We chose Spirit, which we would not recommend because of their despicable baggage fees, but if you wanna go cheap it’s the way to go.

Stay: We stayed with a friend but we recommend AirBnb. Chicago prices are much cheaper than NYC, so you can find a spot in a good neighborhood for cheap.

Get Around: CTA is the best option to get around if you’re staying near a station. The cost is $ for a pass plus $5 for a Ventra card. Also, UberX is a very affordable option in Chicago, with the average trip coming in around $6 from the Westside to the Loop. For two or more people that’s around $2-3 per person, the same cost as transit.

See: The Chicago skyline is amazing, and is a tourist attraction unto itself. Taking the Chicago architecture tour is highly recommended. The Chicago SkyDeck is a bit pricey and is a tourist trap, but the view, including the cantilevered all glass viewing partitions are worth it. Check out the Ebony Fashion Fair exhibit at the Museum of the City of Chicago, and during the warmer months, North Beach is a short walk from downtown Loop.